2-{8 (2,4-Dioxo-1-imidazolidinyl)imino{9 ethyl-P-chlorobenzoate

ABSTRACT

The title compound is a useful anthelmintic.

United States Patent [1 1 [111 3,894,007 White, Jr. 1 July 0, 11975 [54] 2-[(2,4-DIOXO-1- 3,300,510 1/1967 Album et a1 260/309.5

IMIDAZOLIDINYL)IMINO]ETHYL P 3,748,326 7/1973 Schwan 6t 31.... 3,830,805 8/1974 Pllgram 260/309 CHLOROBENZOATE [75] Inventor: Ralph L. White, Jun, Norwich, NY.

[73] Assignee: Morton-Norwich Products, Inc, Norwich, NY.

[22] Filed: Jan. 25, 1974 [21] App]. No.: 436,465

[52] US. Cl. 260/240 G; 260/309.5; 424/273 [51] Int. Cl C0701 49/32 [58] Field of Search 260/240 G, 309.5

[56] References Cited UNITED STATES PATENTS 3,157,645 11/1964 Spencer 260/309.5

OTHER PUBLICATIONS Wagner et 211., Synthetic Organic Chemistry, John Wiley & Sons, N.Y., N.Y., 1953, p. 484.

Primary Examiner-Arthur P. Demers Attorney, Agent, or Firm-Anthony J. Franze ABSTRACT The title compound is a useful anthelmintic.

3 Claims, N0 Drawings 11 2-[(2,4-DlX O-1l- HMHDAZOLHDHNYL)llMlNOETlHlYL-P- CHLQROBENZOATE This invention relates to chemical compounds. More particularly it relates to the compound 2-[(2,4-dioxo-1- imidazolidinyl)imino]ethyl-p-chlorobenzoate (A) and the compound 1-[(2-chloroethylidene)aminojhydantoin useful as an intermediate in the preparation thereof.

The compound (A) is useful as an anthelmintic. When administered per 05 in a dose of 100 mg/kg by gavage as a suspension in aqueous sodium carboxymethyl cellulose to mice harboring the pinworm Syphacia obvelata, reduction of pinworm population is achieved.

In order that this invention may be readily available to and understood by those skilled in the art, the following example of its preparation is set forth:

A. l-[(Z-Chloroethylidene)amin0]hydantoin B. 2-[(2,4-Dioxo-l-imidazolidinyl)imino]ethyl p-Chlorobenzoate In a 2.0 l flask were placed p-chlorobenzoic acid 16 g, 0.10 mole), A. (19 g, 0.10 mole), potassium carbonate (12.0 g), sodium iodide (2.0 g) and acetone (1.01). The stirred mixture was refluxed for five hours and concentrated under reduced pressure to a solid. Water (500 ml) was added and the solution pH was adjusted to pl-l=6 with dilute hydrochloric acid. The resulting solid was collected and air-dried.

Recrystallization from acetonitrile (150 ml) yielded white solid (12 g, 40 percent), m.p. l-l82.

Anal. Calcd. for C l-l ClN O C, 48.74; H, 3.41; N,

Found: C, 48.71; H, 3.48; N, 14.52.

What is claimed is:

1. A compound of the formula:

wherein R is ClCll-l or c1 -CO CH 2. The compound 2-[(2,4-diox0-1- imidazolidinyl )imino]ethyl-p-chlorobenzoate.

3. The compound 1-[(2-chloroethylidene)amino]- 

1. A COMPOUND OF THE FORMULA:
 2. The compound 2-((2,4-dioxo-1-imidazolidinyl)imino)ethyl-p-chlorobenzoate.
 3. The compound 1-((2-chloroethylidene)amino)hydantoin. 